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" He considered. What would he want? A man or a woman? "A woman." How tall? What does she wear? Describe her." Almost as tall as me. Slender - with a nice curvy figure. She's wearing asuit. Her shoes are platforms so that she seems taller than me. She's verypretty, but her hair is cut like a man's." All right. Do you like to be tied up?" I don't know. I've never thought much about that." Do you like to be forced to do something? How about punishment?" Both would excite me." I see. You like to wear panties when you clean the shack. How would youlike to be fully dressed as a maid and clean an apartment?"She did not need his answer. She could SEE the result."I can't help you with the enforcement - or with the punishment. Or rather- I don't want to have anything to do with that. BUT - why don't we bothaccept Helen's offer? We'd go there every Wednesday evening when she'sout. You could be dressed as a proper maid. We spend three hours - cleanher place - collect our pay - then return here.". You?" Me "Keep this to yourself, I did fuck a crossdresser once but I honestly didn't know till he had my dick in his mouth and pulled his out and started walking! (laugh)" T (still uncomfortable but looked intrigued) "Omg what did you do? Are you gay? Or bisexual? So how was it, would you do it again?" Me "Yeah definitely, but I'd prefer a petite one next time so I could dominate and make it a regular thing, that was just a one off" I left it at that, could feel his eyes following me as I put my rubbish in the bin and walked back to the office.. That's when I knew it was on, I'm going to turn this boy into a sissy. Couple of weeks had past, I was making comments here and there about T's tight pants, feminine voice, walk, smell.. Putting my arm on his shoulder when talking and running my hand down his back before walking away etc. Then came that Friday where it went from comments to teasing to confirmed. T was making tea and coffee in the break room, so I went in and told him to.
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